Stadium: Court 13 Round: 19 Ground: Hardcourt outdoor
| Challenger Heilbronn | 2023/06/06 14:35 | Marco Cecchinato v Akira Santillan | 5-7,3-6 |
| Challenger Heilbronn | 2023/06/05 09:30 | Liam Gavrielides v Akira Santillan | 0-6,4-6 |
| Challenger Heilbronn | 2023/06/04 14:00 | Conner Huertas Del Pino v Akira Santillan | 1-6,2-6 |
| ITF M25 Most | 2023/05/25 08:00 | Michael Vrbensky v Akira Santillan | 6-2,6-4 |
| ITF M25 Prague | 2023/05/18 11:00 | Andrew Paulson v Akira Santillan | 2-6,6-3,6-4 |
| ITF M25 Prague | 2023/05/17 08:00 | Akira Santillan v Timo Stodder | 6-2,6-2 |
| Challenger Prague | 2023/05/12 09:00 | Jakub Mensik v Akira Santillan | 3-6,6-3,7-6 |
| Challenger Prague | 2023/05/10 10:55 | Nick Hardt v Akira Santillan | 6-4,4-6,3-6 |
| Challenger Surbiton | 2023/06/06 10:00 | Mark Whitehouse v Zizou Bergs | 6-7,2-6 |
| Challenger Surbiton | 2023/06/05 11:15 | Mark Whitehouse v James McCabe | 6-3,7-5 |
| Challenger Surbiton | 2023/06/04 13:25 | Antoine Bellier v Mark Whitehouse | 4-6,2-6 |
| ITF M25 Varnamo | 2023/05/10 10:40 | Mark Whitehouse v Lucas Catarina | 2-6,1-6 |
| ITF M25 Nottingham | 2023/05/04 09:00 | Mark Whitehouse v George Loffhagen | 4-6,0-6 |
| ITF M25 Nottingham | 2023/05/02 12:40 | Daniel Cox v Mark Whitehouse | 6-7,6-2,6-7 |
| ITF M25 Nottingham | 2023/04/25 10:25 | Christian Sigsgaard v Mark Whitehouse | 6-4,6-1 |
| ITF M25 Nottingham | 2023/04/20 10:15 | Matthew Dellavedova v Mark Whitehouse | 7-6,6-1 |